Water → HCID 68431543, compound

HRID 889257Notes

Reaction equation

HRID 889257 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:21]([CH2:24]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])=CC=1.O.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45].C1(C)C=CC=CC=1>>[C:44]([O:48][C:24](=[O:33])[NH:21][C:10]1[C:14]([F:18])=[CH:15][CH:16]=[CH:17][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 5

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22595558Toluene tert-butyl alcoholHCID 68432333HCID 68432333, compound

Product 1

HCID 68431543HCID 68431543, compound

Procedure

To a solution of 3.2 g (13.0 mmol) of 2-benzyloxy-6-fluorobenzoic acid in 20 mL of tert-butanol/toluene (1:1) is added 2.0 g (19.8 mmol) of triethylamine followed by dropwise addition of 4.6 g (16.7 mmole) of DPPA. The solution is stirred at RT for 15 min. then at 100° C. for 18 h. The mixture is allowed to cool and then is poured into water. The mixture is extracted with ethyl acetate and the solvent from the organic phase is removed under reduced pressure. Methylene chloride is added to the residue and any insoluble material is filtered. The organic solution is passed through a pad of silica gel using methylene chloride to elute the product. The solvent is removed under reduced pressure to give the product as a white solid: mp=103-106° C.; 1H NMR (CDCl3) δ 7.43-7.32 (m, 6H), 7.13-7.06 (m, 1H), 6.78-6.73 (m, 2H), 5.10 (s, 2H), 1.48 (s, 9H).

Workup

  1. waitat 100° C. for 18 h
  2. temperatureto cool
  3. extractionThe mixture is extracted with ethyl acetate
  4. customthe solvent from the organic phase is removed under reduced pressure
  5. additionMethylene chloride is added to the residue
  6. filtrationany insoluble material is filtered
  7. washto elute the product
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-cb3d38203b6845429b8e27e37a030913
Source dataset
uspto-grants-2012_08
Patent number
US08252820B2

Reaction notes

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